Grassy Key vacation rentals

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Top-rated vacation rentals in Grassy Key

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Marathon

4.98 out of 5 average rating, 184 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Aug 2 – 9

G$45,282 GYD per night

Guest favorite

Townhouse in Duck Key

4.98 out of 5 average rating, 141 reviews

3Bd 3Ba Cottage/Village at Hawks Cay/Ocean Views

Our Cottage is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high end finishes, comfy beds and plenty to do in the surrounding areas, the Cottage offers something for everyone. The outdoor green space overlooking the water is gorgeous. Sunsets are amazing right off the screened in lanai. We hope to host you as our guest in the beautiful Florida Keys.

Aug 10 – 17

G$119,799 GYD per night

Superhost

Home in Marathon

4.95 out of 5 average rating, 40 reviews

The Hideaway~Private Pool~Grill~Lush~Tropical!

The Keys Hideaway ~ your private paradise in beautiful Marathon, the heart of the Florida Keys! Gorgeous 3BR home. Your own private pool, gas grill, beach chairs, all await you for your beautiful day in the Florida Keys! Less than 10 min to Sombrero Beach, Dining & Local Bars. We have everything covered for you here at The Hideaway so that you're able to slow down, soak up the sun, and relax! Just another day in Paradise. Experience the Florida Keys like a local and book The Hideaway today!

Sep 8 – 15

G$77,833 GYD per night

Guest favorite

Boat in Islamorada

4.92 out of 5 average rating, 327 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Jan 28 – Feb 4

G$38,963 GYD per night

Guest favorite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 82 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, the Turtle-by-the-Sea Guest Suite is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.

May 25 – Jun 1

G$40,204 GYD per night

Superhost

Villa in Marathon

4.89 out of 5 average rating, 145 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Sep 22 – 29

G$78,776 GYD per night

Guest favorite

Condo in Key Colony Beach

4.97 out of 5 average rating, 196 reviews

Keys Breeze Ocean View Condo & Pool - Key Colony

Gorgeous Florida Keys studio condo in Key Colony Beach with beautiful ocean front location. The condo features all new furniture and furnishings with a crisp, modern interior and kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Condo has one king-sized bed and sleeps 2 people. We just finished a full bathroom remodel adding all new walk-in shower, tile, vanity, etc. This condo is simply exquisite!

Sep 2 – 9

G$58,605 GYD per night

Guest favorite

Cabin in Marathon

4.9 out of 5 average rating, 21 reviews

New Cabins at Bonefish Bay

Make some memories at this unique and family-friendly place. Bring the family or just a romantic get away to enjoy the Keys. These new cabins have all your needs. Full bathroom and kitchen. Cozy but spacious. We also have boat ramp and dock space so you can bring your boats and water toys. We are located in the middle of the Florida Keys and easy access to all attractions and restaurants. We do have a big pool, bikes, and kayaks for our guests to use during their stay.

Sep 5 – 12

G$34,664 GYD per night

Guest favorite

Home in Marathon

5.0 out of 5 average rating, 10 reviews

Million Dollar View

Take it easy at this unique and tranquil getaway. Enjoy endless open water views from anywhere on this acre-sized, OCEAN FRONT Gulf-side estate. Coconut palms, private hot tub & pool, boat ramp, and a 285 foot long private pier great for catching fish and spectacular sunsets. Like a private resort, you can play giant chess on the beach, win at ping pong, take out a kayak, or paddle board or stroll through fabulous gardens with no staff to tip. License VACA-23-190

Dec 7 – 14

G$203,037 GYD per night

Guest favorite

Home in Marathon

4.97 out of 5 average rating, 32 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

You don't come to the islands to stay in a town! Relax in our tropical paradise beach home away from the traffic and noise of US Hwy #1. The perfect location has now been turned into the perfect oasis. Special features include a gourmet kitchen, private pool surrounded by lush landscaping, private 300' pier/dock with a fish cleaning station. Our guests enjoy luxury bedding with quality linens, fluffy towels and bathrobes. Wireless internet service and cable tv.

Apr 19 – 26

G$129,868 GYD per night

Guest favorite

Home in Marathon

4.96 out of 5 average rating, 124 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Oct 10 – 17

G$70,913 GYD per night

Superhost

Apartment in Marathon

4.86 out of 5 average rating, 94 reviews

Cozy Keys Efficiency 8a

Efficiency has a queen size bed, a 3-seat leather sofa and a small dining table with 2 chairs. Private bathroom. Mini split ductless cooling AC. Kitchen is fully equipped with 4 burner stove, microwave, medium size refrigerator with freezer. Enjoy the breezes on your patio, each unit has a gas BBQ grill and a picnic bench outside. Enjoy a swim in our shared pool. Pricing include 12.5 % tax Efficiency has a 2 person maximum occupancy - no exceptions.

Oct 25 – Nov 1

G$43,140 GYD per night